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Extend Your Vacation With These Fun Stops on Route 50

Extend Your Vacation With These Fun Stops on Route 50

beach entrance

Your Ocean City or Assateague vacation will come to an end eventually, but don’t despair! Maryland’s Eastern Shore offers a variety of engaging ways to extend your trip home as you travel home. We’re sharing eight fun stops on Route 50 to keep your vacation vibes alive and well!

Explore a small town

Four Maryland Main Street communities line Route 50, providing travelers multiple opportunities to get out of the car and explore the Eastern Shore. Each small town has its own unique charm, where you can enjoy art, culture, history, local food, and shops in an authentic setting.


Perhaps best known nationally as the setting for films Runaway Bride and Tuck Everlasting, Berlin has plenty to occupy you for either a quick stop or an overnight visit.

mermaid museum bathtub
Credit: @san__zu

Some highlights: visit the Mermaid Museum, enjoy a beer at Burley Oak Brewing Company, and take a selfie on the porch of the 1895 Hotel Atlantic.


Home of the Salisbury University Sea Gulls, Salisbury is a designated arts and entertainment district with a variety of shops and eating establishments lining Main Street. You can also take a stroll on the Riverwalk lining the scenic Wicomico River, meander the Labyrinth, and catch a show in the amphitheater


One of the oldest colonial cities in Maryland, Cambridge has a rich maritime history that can still be experienced today. Located off the Choptank River, Cambridge has something for everyone – choose a walking tour of the Chesapeake Country Mural Trail or a bite at one of the town’s locally-owned restaurants in the historic downtown. 

Hands holding a meatball sandwich
Photo Credit: Chris Vandergrift

Our recommendation: the meatballs at Ava’s, which has a St. Michaels and Cambridge location.


One of the top ten small towns in America, Easton is an arts and culture hub with restaurants, pubs, galleries, shopping, and walking trails galore.

Easton, MD
Photo Credit: via

There are a variety of overnight options if you wish to extend your stay.

Catch a game

The Delmarva Shorebirds play all summer at Arthur W. Perdue Stadium in Salisbury, so plan a trip to the ballpark after your OC stay. An Orioles single-A affiliate, the Shorebirds offer high-quality baseball at an affordable price, along with family-friendly themes and game day promotions.

Visit some animals

Also in Salisbury is the Salisbury Zoological Park, a free zoo housing over 100 animals, including adorable Andean bears. Your family can get up-close-and-personal with a variety of mammals, birds, and amphibians, and grab a meal at the Beastro Cafe.

Wooden playground with red roofs
Photo Credit: Ben’s Red Swings Community Playground

Keep the fun going with a run around on the impressive playground right next to the zoo.

Hike in nature

Located south of Cambridge, the Blackwater National Wildlife Refuge is a 32,000 acre sanctuary for birds migrating along the Atlantic Flyway. Home to a large population of bald eagles, five miles of hiking, and 17 miles of paddling, the Refuge is a perfect way to combat car fatigue.

Stop at a farmer’s market

Stock up on Eastern Shore corn, berries, peaches, and veggies at one of the roadside stands lining Route 50. Oakley’s Farm Market in Hebron and Wright’s Market in Mardela Springs are two of the largest and most popular, but don’t overlook smaller farm stands, where the produce is just as delicious.

See some history

The Eastern Shore has a plethora of history. The largest historic site is the Harriet Tubman Underground Railroad National Historical Park, which consists of a museum and a driving tour of sites commemorating Tubman’s bravery. 

Other historic sites require some seeking out. Fortunately, two heritage areas —Beach to Bay and Heart of Chesapeake County—have comprehensive websites with maps and trip suggestions.

Shop at the outlets

If you didn’t have time to shop the Ocean City outlets, you have another chance! The Queenstown Outlets offer popular shops like Aeropostale, Coach, Nike, Old Navy, UnderArmour and more.

Eat seafood

Savor the bounty of the Chesapeake Bay once last time with a stop at Harris Crab House in Kent Narrows. Besides hard shells, they offer a full menu of seafood, steaks, chicken, and sandwiches. But don’t stop there…

Explore Kent Island

Chances are you’ve passed Kent Island at least once if not half a dozen times and thought, I should stop and explore the area sometime. It’s worth the stop.

two white Adirondack chairs
Photo Credit: Stephanie Verni

Pop into cute boutiques, visit a winery that got its start from a sweet love story, take a bike ride, or squish your toes in the sand one last time.

Lead Photo: Susan Moynihan

About the Author

Heidi Glatfelter Schlag is a marketer, history lover, and traveler who can often be found exploring museums, parks, small towns, and farms. She founded Culture-Link Communications, where she helps local nonprofits and small businesses build their brands. Heidi lives in Frederick, MD, with her husband and two dogs.

Maryland Road Trips is a part of Postern Publishing.
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